The advertising industry is undergoing a revolution thanks to the development of digital media. Digital out-of-home (DOOH) advertising is part of this revolution. It refers to digital media used for marketing purposes in public and outdoor locations. The industry is growing by about 40% per year and is expected to reach US $7 billion annually. This thesis project aims to create a deeper level of interaction with DOOH audiences through environmental data analytics. The project allows the advertising team to create a display wherein the billboard content changes automatically and synchronically with changes in the display’s environment. Since digital out-of-home (DOOH) offers a market of absolute growth, I am also investigating how to introduce and launch this interactive solution to the DOOH advertising Industry. This plan is for the start-up of SunDOOH Consulting in Toronto, Canada and serves major U.S. market.